Sodium Bicarbonate → HCID 10737331, compound

HRID 129018Notes

Reaction equation

HRID 129018 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])=[C:6]([CH3:13])[N:5]=[C:4]([CH3:14])[N:3]=1.Cl.[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>C(O)CCC>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])=[C:6]([CH3:13])[N:5]=[C:4]([CH3:14])[N:3]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27240964-Bromobenzylamine hydrochlorideHCID 107272924-Chloro-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine

Product 1

HCID 10737331HCID 10737331, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-chloro-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine (3.00 g, 0.0141 mol), 4-bromobenzylamine hydrochloride (3.45 g, 0.0155 mol), NaHCO3 (2.37 g, 0.0282 mol), and n-butanol (20 mL) was heated under reflux for 70 h. The mixture was concentrated, taken up in EtOAc, washed with water, dried MgSO4), and concentrated. Trituration with ether/hexane gave 2.84 g (56%) of product as a white solid. An analytical sample was recrystallized from ether/hexane, mp 111°-113° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 70 h
  3. concentrationThe mixture was concentrated
  4. washwashed with water, dried MgSO4), and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eafd00197993429ea57037ed10087ebc
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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